Hydrazine hydrate (1:1) → HCID 21975635, compound

HRID 2352901Notes

Reaction equation

HRID 2352901 reaction equation
[F:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:3]1.O.NN>C(O)C.[Ni]>[F:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68696157HCID 68696157, compound

Product 1

HCID 21975635HCID 21975635, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of crude 3-Fluoro-1-[3-(4-nitro-phenoxy)-propyl]-pyrrolidine (6.316 g, ˜24 mmol) was dissolved in absolute ethanol (180 mL) and to this solution was added hydrazine monohydrate (˜7.9 mL) followed by the addition of a small portion of Raney nickel (˜1 mL). The reaction mixture was heated to 50° C. with stirring for ˜2 h at which point all gas evolution had ceased. The reaction mixture was filtered through celite to remove the Raney nickel. The filtrate was concentrated in vacuo to give 4-[3-(3-Fluoro-pyrrolidin-1-yl)-propoxy]-phenylamine as a brown oil which was subjected to flash silica gel chromatography (CHCl3 to CHCl3:MeOH, 1:40 gradient eluant). Pure 4-[3-(3-Fluoro-pyrrolidin-1-yl)-propoxy]-phenylamine was isolated as a reddish oil (4.033 g, 79%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customto remove the Raney nickel
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9a976ba24b094914a50ed82ce1c95dd7
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

Loading…